Search Hotels in Oakland, Chicago

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Our top choices for Oakland hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 4.7 mi from Oakland
9.4 out of 10, Exceptional, (2,455 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is £220
includes taxes & fees
26 Apr - 27 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 4.1 mi from Oakland
8.6 out of 10, Excellent, (2,376 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is £157
includes taxes & fees
9 May - 10 May
Palmer House a Hilton Hotel

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 4.5 mi from Oakland
9.4 out of 10, Exceptional, (3,496 reviews)
"Increíble hotel súper friendly staff! "
United States
Alejandra
The price is £239
includes taxes & fees
9 May - 10 May
Hyatt Regency Chicago

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 5.8 mi from Oakland
8.2 out of 10, Very good, (1,360 reviews)
"Very beautiful place to stay"
United States
angie
The price is £97
includes taxes & fees
26 Apr - 27 Apr
The Chicago Hotel Collection Ambassador Gold Coast

River Hotel

River Hotel
4.0 star property
The Loop, 4.6 mi from Oakland
8.8 out of 10, Excellent, (5,077 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is £94
includes taxes & fees
28 Apr - 29 Apr
River Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 3.7 mi from Oakland
8.0 out of 10, Very good, (10,095 reviews)
"The stay is well worth the affordable price."
United States
Thomas
The price is £108
includes taxes & fees
26 Apr - 27 Apr
Congress Plaza Hotel

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 4.4 mi from Oakland
8.8 out of 10, Excellent, (2,115 reviews)
"lovely hotel "
United States
alyvia
The price is £235
includes taxes & fees
25 Apr - 26 Apr
Fairmont Chicago at Millennium Park

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 4.2 mi from Oakland
9.2 out of 10, Wonderful, (2,236 reviews)
"Great stay!"
United States
Jessica
The price is £155
includes taxes & fees
16 Apr - 17 Apr
Silversmith Hotel Chicago Downtown

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
4.4 mi from Oakland
8.6 out of 10, Excellent, (1,908 reviews)
"Overall a great stay."
United States
Joshua
The price is £210
includes taxes & fees
9 May - 10 May
Radisson Blu Aqua Hotel Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 4.9 mi from Oakland
8.6 out of 10, Excellent, (3,168 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is £99
includes taxes & fees
26 Apr - 27 Apr
Aloft Chicago Mag Mile

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 4.6 mi from Oakland
9.4 out of 10, Exceptional, (3,373 reviews)
"I loved my stay"
United States
Janet
The price is £147
includes taxes & fees
26 Apr - 27 Apr
The Royal Sonesta Chicago Downtown

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 3.6 mi from Oakland
8.6 out of 10, Excellent, (2,729 reviews)
"We love staying here "
United States
Carrie
The price is £195
includes taxes & fees
8 May - 9 May
Hilton Chicago

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 4.5 mi from Oakland
9.6 out of 10, Exceptional, (3,900 reviews)
"Loved the stay here !"
United States
Alisha
The price is £133
includes taxes & fees
26 Apr - 27 Apr
L7 Chicago by LOTTE

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 5.1 mi from Oakland
8.8 out of 10, Excellent, (2,159 reviews)
"Nice place to stay. "
United States
Akanksha
The price is £128
includes taxes & fees
10 May - 11 May
The Godfrey Hotel Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 4.6 mi from Oakland
8.8 out of 10, Excellent, (2,174 reviews)
"Great stay!"
United States
Hannah
The price is £101
includes taxes & fees
28 Apr - 29 Apr
Club Quarters Hotel Wacker at Michigan, Chicago

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 3.4 mi from Oakland
8.8 out of 10, Excellent, (1,948 reviews)
"Hotel was really nice"
United States
LaCarr
The price is £103
includes taxes & fees
27 Apr - 28 Apr
Hilton Garden Inn Chicago Downtown South Loop

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
4.5 mi from Oakland
9.0 out of 10, Wonderful, (3,254 reviews)
"Excellent stay."
United States
Fenton
The price is £229
includes taxes & fees
15 Apr - 16 Apr
Swissotel - Chicago

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 4.5 mi from Oakland
9.4 out of 10, Exceptional, (4,280 reviews)
"Loved it, would stay here everytime"
United States
KARELY
The price is £125
includes taxes & fees
30 Apr - 1 May
citizenM Chicago Downtown

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 4.9 mi from Oakland
9.4 out of 10, Exceptional, (3,802 reviews)
"Great hotel "
United States
Marina
The price is £133
includes taxes & fees
26 Apr - 27 Apr
Hotel Riu Plaza Chicago

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 4.3 mi from Oakland
9.4 out of 10, Exceptional, (1,044 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is £138
includes taxes & fees
26 Apr - 27 Apr
Staypineapple, An Iconic Hotel, The Loop
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

O'Hare

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Top Oakland Hotel Reviews

Frequently asked questions

What are the best hotels in Oakland that travellers recommend?
Two of the best hotels in Oakland that receive consistently high recommendations from travellers are the Sophy Hyde Park and the Hyatt Place Chicago-South/University Medical Center.

Sophy Hyde Park is a 4-star hotel with an outstanding 9.6 rating. Guests frequently compliment the friendly and great staff, the comfortable and clean rooms, and the convenient location. The hotel provides bathrobes and premium bedding, ensuring a comfortable stay.

Another highly recommended option is the 3-star Hyatt Place Chicago-South/University Medical Center, which has an 8.8 rating. Customers often highlight the friendly and helpful staff, the great location, and the fresh and good breakfast. The hotel offers spacious and clean rooms, an indoor pool, and connecting rooms, making it suitable for families.
What are the best family hotels in Oakland?
For family-friendly hotels in Oakland, consider the Hyatt Place Chicago-South/University Medical Center or the Sophy Hyde Park.

The 3-star Hyatt Place Chicago-South/University Medical Center, with an 8.8 rating, is an excellent choice for families. Guests frequently mention the friendly and helpful staff, the spacious and clean rooms, and the fresh and good breakfast. It offers amenities like connecting rooms, sofa beds, a child-friendly window design, kids' meals, and free cribs. It is also conveniently located near attractions such as Jackson Park and the 57th Street Beach.

Another highly recommended option is the 4-star Sophy Hyde Park, which boasts an impressive 9.6 rating. This hotel is praised by guests for its friendly staff, comfortable and clean rooms, and convenient location. Family amenities include free cribs, a child-friendly window design, connecting rooms, and free toiletries. It is also close to recreational areas like Jackson Park and Washington Park.
What are the top pet-friendly hotels in Oakland?
For top pet-friendly hotels in Oakland, Illinois, consider the Sophy Hyde Park and the Hyatt Place Chicago-South/University Medical Center.

The 4-star Sophy Hyde Park, with an excellent 9.6 rating, is a fantastic choice for travellers with dogs. Guests consistently praise the friendly and great staff, comfortable and clean rooms, and convenient location. It is also close to several green spaces, including Jackson Park (2.5 km), Paul H. Douglas Nature Sanctuary (1.5 km), and Washington Park (1.7 km), great for walks with your pet.

Another highly-rated option is the 3-star Hyatt Place Chicago-South/University Medical Center, holding an 8.8 rating. This hotel also permits pets and offers spacious and clean rooms. Travellers often highlight the friendly and helpful staff, the great location, and the fresh and good breakfast. It is similarly close to outdoor areas like Paul H. Douglas Nature Sanctuary (1.4 km) and Garden of the Phoenix (1.6 km).
What are the best budget hotels in Oakland?
For a highly-rated budget hotel in Oakland, consider the Hyatt Place Chicago-South/University Medical Center.

This 3-star hotel has an impressive 8.8 rating and offers excellent value. Guests frequently praise the friendly and helpful staff, the good location, and the fresh and tasty breakfast. The rooms are described as spacious and clean, and parking is noted as easy and excellent. Key amenities include free WiFi, free cribs, and a complimentary area shuttle. It is conveniently located near several points of interest, such as the Hyde Park Art Centre, which is just 0.4 km away, and the Barack Obama Residence, 0.9 km away.
What are the most romantic hotels in Oakland for couples?
For a romantic couples' stay in Oakland, the Sophy Hyde Park is an excellent choice.

This 4-star hotel, with an impressive 9.6 rating, offers a delightful experience for couples. Guests frequently praise its comfortable and clean rooms, as well as the friendly and great staff. The hotel provides couples dining options, complimentary toiletries, and free WiFi, ensuring a pleasant and convenient stay. Its location is considered great and convenient, with several points of interest nearby, such as the Hyde Park Art Centre, just 0.6 km away, and the historic Robie House, 1.1 km from the hotel. The Sophy Hyde Park also features a great bar and comfortable beds, contributing to a relaxing and enjoyable escape.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Oakland.
How can I save on a Oakland hotel booking with Expedia?
Members always get our best prices. Find our best Oakland hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Oakland hotel?
Hotel prices in Oakland often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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